Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Chiral Silver Complex-Catalyzed Diastereoselective and Enantioselective Michael Addition of 1-Pyrroline-5-carboxylates to α-Enones

Chiral Silver Complex-Catalyzed Diastereoselective and Enantioselective Michael Addition of 1-Pyrroline-5-carboxylates to α-Enones
Masato Harada, Shin-ichi Fukuzawa, Akihiro Koizumi, Ryosuke Haraguchi
A AgOAc/ThioClickFerrophos complex-catalyzed the highly diastereo- and enantioselective reaction between 1-pyrroline-5-carboxylates (1) and acyclic α-enones (2) in MeOH, in the presence of DBU, to give the single isomer Michael adducts (3) in high yields (up to 99%) with excellent enantioselectivies (up to 99% ee). Subsequent reduction of the Michael adducts with sodium cyanoborohydride successfully produced the fused pyrrolizidine ester as an almost pure single stereoisomer.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01335

DOI: 10.1021/acs.joc.7b01335

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